Acetic Acid → 7-methoxy-6-(2-methoxyethoxy)quinazolin-4(3H)-one

HRID 871277Notes

Reaction equation

HRID 871277 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]([O:12][CH3:13])[C:9]([O:14][CH2:15][CH2:16][O:17][CH3:18])=[CH:8][C:3]=1[C:4](OC)=[O:5].CC(O)=O.[CH:23]([NH2:25])=O>>[CH3:13][O:12][C:10]1[CH:11]=[C:2]2[C:3]([C:4](=[O:5])[NH:25][CH:23]=[N:1]2)=[CH:8][C:9]=1[O:14][CH2:15][CH2:16][O:17][CH3:18]

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 713FormamideHCID 58394329Methyl 2-amino-4-methoxy-5-(2-methoxyethoxy)benzoate

Product 1

HCID 1355098047-methoxy-6-(2-methoxyethoxy)quinazolin-4(3H)-oneYield 69%

Conditions

Temperature
140 °C

Procedure

According to the procedure described in Example 6A Step 4, a mixture of methyl 2-amino-4-methoxy-5-(2-methoxyethoxy)benzoate (3.05 g, 11.9 mmol) and AcOH (5.4 mL) in formamide (15.25 mL) was heated at 140° C. overnight, to afford 7-methoxy-6-(2-methoxyethoxy)quinazolin-4(3H)-one as a solid (2.07 g, 69%). 1H NMR (300 MHz, DMSO-d6) δ 12.0 (br, 1H), 7.99 (s, 1H), 7.45 (s, 1H), 7.14 (s, 1H), 4.19 (t, 2H), 3.91 (s, 3H), 3.71 (t, 2H), 3.32 (s, 3H).

Sources & evidence

ORD record
ord-55af03aadce54d3d880e78316a45918d
Source dataset
uspto-grants-2015_03
Patent number
US08969587B2

Reaction notes

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